US 4,071,497 AGranted

Hindered hydroxyphenylalkanoates of thioether isopropanols and stabilized compositions

AssigneeCiba-Geigy Corporation

InventorsMartin Dexter, David Herbert Steinberg

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Abstract

The compounds are esters having the formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently alkyl, cycloalkyl, alkylthioethyl or alkylpolyoxyalkylene, Z is oxygen or sulfur, R.sub.3 is the group ##STR2## R.sub.4 is hydrogen, alkyl, cycloalkyl or .alpha.-methylbenzyl, R.sub.5 is alkyl or cycloalkyl, R.sub.6 is hydrogen or alkyl and, provided when R.sub.4 is hydrogen, R.sub.6 is alkyl and R.sub.5 is located on the carbon atom ortho to the hydroxyl group, and A is a covalent carbon bond or lower alkylene. The esters of this invention are prepared by usual esterification procedures from a thioether isopropanol and an acid of formula ##STR3## or a derivative thereof, preferably the methyl ester. The thioether isopropanols are prepared by reaction of epichlorohydrin with an alcohol or mercaptan followed by the opening of the oxirane ring with a mercaptide to give the desired thioether isopropanol. The compounds are useful as stabilizers for organic materials, especially polyolefins, which degrade upon exposure to light and heat.

Claims12

Dependent claims

A stabilized composition of matter comprising a polyolefin and from 0.01 to 5% by weight of a stabilizing compound of the formula ##STR15## wherein R.sub.1 and R.sub.2 are each independently alkyl of 1 to 30 carbon atoms, cycloaklyl of 5 to 12 carbon atoms, alkylthioethyl of 4 to 27 atoms in the chain or alkyl polyoxyalkylene of 4 to 27 atoms in the chain having the general structure R.degree.(OC.sub.n H.sub.2n).sub.h or R.degree.(OCH.sub.2 CHR').sub.h where R.degree. is alkyl of 1 to 18 carbon atoms, n is 2 to 4, R' is hydrogen, methyl or ethyl and h is 1 to 3,

Z is oxygen or sulfur,
R.sub.3 is the group ##STR16## R.sub.4 is hydrogen, alkyl of 1 to 8 carbon atoms, cycloakyl of 5 to 6 carbon atoms or .alpha.-methylbenzyl,
R.sub.5 is alkyl of 1 to 8 carbon atoms or cycloalkyl of 5 to 6 carbon atoms,
R.sub.6 is hydrogen or lower alkyl of 1 to 4 carbon atoms, or R.sub.4 and R.sub.6 together are a butylene chain which, together with the phenyl ring, form a tetrahydronaphthyl group, and provided when R.sub.4 is hydrogen, R.sub.6 is alkyl and R.sub.5 is located on the carbon atom ortho to the hydroxyl group, and
A is a covalent carbon bond or a straight or branched lower alkylene having 1 to 8 carbon atoms.

2 more elements

Dependencies are inferred from the claim text.